I would go through Hacker news past posts, and comments. Print out the better ones. Get him familiar with the lingo. My biggest stumbling block was learning

I would go through Hacker news past posts, and comments. Print out the better ones. Get him familiar with the lingo. My biggest stumbling block was learning the ever changing language of all aspects of computing. Then buy him Learn to Program by Chris Pine. I would also want him very comfortable with UNIX, and the command line. When he gets out,if he has some support; he will do just fine.